Methods for controlling undesirable plant species with benzodiazepine compounds

ABSTRACT

There are provided methods for controlling undesirable plant species with benzodiazepine compounds of formulas I and II ##STR1## Further provided are herbicidal compositions comprising those compounds.

BACKGROUND OF THE INVENTION

Weeds cause tremendous global economic losses by reducing crop yieldsand lowering crop quality. In the United States alone, agronomic cropsmust compete with hundreds of weed species. Moreover, some crop damagedue to inadvertent overexposure to certain herbicides used to controlundesirable plant species has occurred.

Accordingly, there is ongoing research to discover and develop moreeffective herbicidal agents for the selective control of weeds in thepresence of crops. If successful, inadvertent overexposure to suchagents will cause less crop damage, and perhaps eliminate such damagealtogether.

Certain benzodiazepine compounds are known to possess antianxiety,antibiotic, blood pressure-lowering, respiratory-depressing, antiataxiaand/or anticonvulsant activity (see, e.g., U.S. Pat. Nos. 3,681,341,3,947,408, 3,985,732, 4,031,079, 4,185,016, 4,316,839, 4,352,815,4,352,817 and 4,772,599; W. B. Wright, Jr., et al, Journal of MedicinalChemistry, 21, pp. 1087-1089 (1978); P. J. McCloskey and A. G. Schultz,Journal of Organic Chemistry, 53, pp. 1380-1383 (1988); T. T. Tita andM. J. Kornet, Journal of Heterocyclic Chemistry, 24, pp. 409-413 (1987);M. Mori, et al, Tetrahedron, 42, pp. 3793-3806 (1986); T. Nagasaka, etal, Tetrahedron Letters, 30, pp. 1871-1872 (1989); A. G. Schultz, et al,Journal of the American Chemical Society, 109, pp. 6493-6502 (1987); E.Wolf and H. Kohl, Liebigs Ann. Chem., pp. 1245-1251 (1975); A. Kamal,Journal of Organic Chemistry, 56, pp. 2237-2240 (1991); R. Singh, et al,Indian Journal of Chemistry, 20B, pp. 129-131 (1981); and A. E. Azzouny,et al, Pharmazie, 32, pp. 318-323 (1977)).

However, no herbicidal utility for the benzodiazepine compounds isdisclosed or suggested in those patents and publications.

It is an object of the present invention to provide a method forcontrolling undesirable plant species with benzodiazepine compounds.

It is also an object of the present invention to provide a method forthe selective control of undesirable plant species growing in thepresence of cereal crops using those compounds.

It is yet another object of the present invention to provide herbicidalcompositions containing those benzodiazepine compouns. These and otherobjects of the present invention will become more apparent from thedetailed description thereof set forth below.

SUMMARY OF THE INVENTION

The present invention provides a method for controlling undesirableplant species which comprises applying to the foliage of said plants orto the soil, water or other medium water containing seeds or otherpropagating organs there-of, a herbicidally effective amount of abenzodiazepine compound having the structural formula ##STR2## wherein Xis hydrogen, halogen, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄haloalkoxy, C₂ -C₃ alkenyl, C₂ -C₃ alkynyl, CO₂ R₅, C(O)NR₆ R₇, S(O)_(m)R₈, C(O)R₉, or benzyl optionally substituted with one or more halogen,nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄haloalkoxy groups;

X₁ is hydrogen, halogen, methyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄haloalkoxy, C₂ -C₅ alkynyl, CO₂ R₅, C(O)NR₆ R₇, S(O)_(m) R₈, C(O)R₉, orbenzyl optionally substituted with one or more halogen, nitro, cyano, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy group;

X₂ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₂ -C₃alkenyl, C₂ -C₃ alkynyl, CO₂ R₅, C(O)NR₆ R₇, S(O)_(m) R₈, C(O)R₉, orbenzyl optionally substituted with one or more halogen, nitro, cyano, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups;

X₃ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy, C₂-C₃ alkenyl, C₂ -C₃ alkynyl, CO₂ R₅, C(O)NR₆ R₇, S(O)_(m) R₈, C(O)R₉, orbenzyl optionally substituted with one or more halogen, nitro, cyano, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups;

R₅ is hydrogen, C₁ -C₄ alkyl, benzyl optionally substituted with one ormore halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy or C₁ -C₄ haloalkoxy groups, or an alkali metal, alkaline earthmetal, manganese, copper, zinc, cobalt, silver, nickel, ammonium ororganic ammonium cation;

R₆ and R₇ are each independently C₁ -C₄ alkyl, benzyl optionallysubstituted with one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups, phenyl optionallysubstituted with one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups, or R₆ and R₇ aretaken together to form a ring in which R₆ R₇ is represented by--(CH₂)_(n) -- where n is an integer of 2, 3, 4 or 5;

m is an integer of 0, 1 or 2;

R₈ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, NR₁₀ R₁₁, OR₁₂ or phenyloptionally substituted with one or more halogen, nitro, cyano, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups;

R₁₀ and R₁₁ are each independently hydrogen, C₁ -C₄ alkyl, benzyloptionally substituted with one or more halogen, nitro, cyano, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups,phenyl optionally substituted with one or more halogen, nitro, cyano, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups,or R₁₀ and R₁₁ are taken together to form a ring in which R₁₀ R₁₁ isrepresented by --(CH₂)_(q) -- where q is an integer of 2, 3, 4 or 5;

R₁₂ is hydrogen or C₁ -C₄ alkyl;

R₉ is hydrogen, C₁ -C₄ alkyl or phenyl optionally substituted with oneor more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy or C₁ -C₄ haloalkoxy groups;

A, A₁ and W are each independently O or S with the proviso that when A₁is S then A is O;

R is C₃ -C₆ cycloalkyl, C₂ -C₅ alkenyl, C₂ -C₅ alkynyl, C₁ -C₅ alkyloptionally substituted with one CO₂ R₁₃ group, one phenyl groupoptionally substituted with one or more halogen, nitro, cyano, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups, orone 5- or 6-membered heterocycle group containing one to three nitrogenatoms, one oxygen atom and/or one sulfur atom and two to five carbonatoms optionally substituted with one or more halogen, nitro, cyano, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups,phenyl optionally substituted with one or more halogen, nitro, cyano, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groupswith the proviso that the para-position of the phenyl ring is notsubstituted, a 5- or 6-membered heterocycle group containing one tothree nitrogen atoms, one oxygen atom and/or one sulfur atom and two tofive carbon atoms optionally substituted with one or more halogen,nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C.sub. 1-C₄ haloalkoxy groups, or R may be taken together with R₁ and the atomsto which they are attached to form a five membered saturated ringsubstituted with one to three C₁ -C₄ alkyl groups;

R₁₃ is hydrogen, C₁ -C₄ alkyl, benzyl optionally substituted with one ormore halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy or C₁ -C₄ haloalkoxy groups, or an alkali metal, alkaline earthmetal, manganene, copper, zinc, cobalt, silver, nickel, ammonium ororganic ammonium cation;

R₁ and R₂ are each independently hydrogen, methyl, ethyl, or R₁ may betaken together with R and the atoms to which they are attached to form afive membered saturated ring substituted with one to three C₁ -C₄ alkylgroups, and when taken together, R₁ and R₂ may form a ring in which R₁R₂ is represented by --(CH₂)_(t) -- where t is an integer of 2, 3, 4, 5or 6 with the proviso that when R₁ is methyl or ethyl then R₂ ishydrogen;

R₃ is hydrogen, C₁ -C₄ alkyl or hydroxy with the proviso that when R₃ ishydroxy, X₂ is other than C₁ -C₄ alkyl, and further with the provisothat when R₃ is C₁ -C₄ alkyl, X₁ is other than hydrogen or methyl; and

R₄ is C₁ -C₆ alkyl, C₃ -C₆ cycloalkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkenyl,C₂ -C₆ alkynyl, benzyl optionally substituted with one or more halogen,nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄haloalkoxy groups, or phenyl optionally substituted with one halogen,nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄haloalkoxy group;

and the optical isomers and diastereomers thereof;

and mixtures thereof.

This invention also relates to a method for the selective control ofundesirable plant species in the presence of cereal crops using thosecompounds.

This invention also relates to herbicidal compositions comprising thosecompounds and an agronomically acceptable carrier.

DETAILED DESCRIPTION OF THE INVENTION

The present invention provides a method for controlling undesirableplant species which comprises applying to the foliage of said plants orto the soil, water,or other medium containing seeds or other propagatingorgans thereof, a herbicidally effective amount of a formula I or IIbenzodiazepine compound.

The present invention also provides methods and compositions for theselective control of undesirable plant species in the presence of cerealcrops which comprises applying to the foliage and stems of the crops andundesirable plant species growing in the presence thereof or to thesoil, water, or other medium containing seeds or other propagatingorgans of the undesirable plant species in which the crops are growing,an amount of a formula I or II benzodiazepine compound effective for theselective control of the undesirable plant species growing in thepresence of the crops.

The benzodiazepine compounds useful in the methods and compositions ofthe present invention have the structural formula ##STR3## wherein X,X₁, X₂, X₃, A, A₁, W, R, R₁, R₂, R₃ and R₄ are as described hereinabove.

Preferred benzodiazepine herbicidal agents of the present invention arethose wherein

X and X₂ are hydrogen;

X₁ is hydrogen, halogen, methyl, C₁ -C₄ alkoxy or C₂ -C₃ alkynyl;

X₃ is hydrogen or methyl;

A is O;

A₁ and W are each independently O or S;

R is C₃ -C₆ cycloalkyl, C₁ -C₅ alkyl, phenyl optionally substituted withone or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁-C₄ alkoxy or C₁ -C₄ haloalkoxy groups with the proviso that thepara-position of the phenyl ring is not substituted, or R may be takentogether with R₁ and the atoms to which they are attached to form a fivemembered saturated ring substituted with one to three C₁ -C₄ alkylgroups;

R₁ and R₂ are hydrogen or R₁ may be taken together with R and the atomsto which they are attached to form a five membered saturated ringsubstituted with one to three C₁ -C₄ alkyl groups;

R₃ is hydrogen or hydroxy; and

R₄ is C₁ -C₆ alkyl, C₃ -C₆ cycloalkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkenyl,C₂ -C₆ alkynyl, benzyl optionally substituted with one or more halogen,nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄haloalkoxy groups, or phenyl optionally substituted with one halogen,nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄haloalkoxy group.

More preferred herbicidal agents of the present invention are thosewherein

X, X₂, X₃, R₂ and R₃ are hydrogen;

X₁ is hydrogen, halogen or methyl;

A, A₁ and W are 0;

R is C₃ -C₆ cycloalkyl, C₁ -C₅ alkyl, or R may be taken together with R₁and the atoms to which they are attached to form a five memberedsaturated ring substituted with one to three C₁ -C₄ alkyl groups;

R₁ is hydrogen or R₁ may be taken together with R and the atoms to whichthey are attached to form a five membered saturated ring substitutedwith one to three C₁ -C₄ alkyl groups; and

R₄ is C₁ -C₆ alkyl.

Benzodiazepine compounds which are particularly effective herbicidalagents include

7-chloro-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione;

7-chloro-1,2,3,11a-tetrahydro-3,3-dimethyl-5H-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11(10H)-dione;

7-chloro-1,2,3,11a-tetrahydro-2,3,3-trimethyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione;

4-tert-butyl-3,4-dihydro-7-methyl-1H-1,4-benzodiazepine-2,5-dione;

7-chloro-3,4-dihydro-4-(2,2-dimethylpropyl)-1H-1,4-benzodiazepine-2,5-dione;

1,2,3,11a-tetrahydro-3,3,7-trimethyl-5H-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11(10H)-dione;

7-bromo-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione;

4-tert-butyl-3,4-dihydro-7,9-dimethyl-1H-1,4-benzodiazepine-2,5-dione;

4-tert-butyl-7-chloro-3,4-dihydro-2-thio-1H-1,4-benzodiazepine-2,5-dione;

4-tert-butyl-7-chloro-3,4-dihydro-9-methyl-1H-1,4-benzodiazepine-2,5-dione;and

4-tert-butyl-7-chloro-3,4-dihydro-2-methoxy-5H-1,4-benzodiazepin-5-one,among others.

Exemplary of halogen hereinabove are fluorine, chlorine, bromine andiodine. The term "C₁ -C₄ haloalkyl" is defined as a C₁ -C₄ alkyl groupsubstituted with one or more halogen atoms. The term "C₁ -C₄ haloalkoxy"is defined as a C₁ -C₄ alkoxy group substituted with one or more halogenatoms. In formulas I and II above, alkali metals include: sodium,potassium and lithium. Alkaline earth metals of formulas I and IIinclude magnesium and calcium. Further, the term "organic ammonium"contemplates agronomically acceptable substituents and may be defined asa group consisting of a positively charged nitrogen atom monovalentlyjoined to from one to four aliphatic hydrocarbon groups, each containingfrom one to sixteen carbon atoms. Examples of other "medium" in whichplants grow include hydroponics, synthetic polymer substrates, etc.

Certain benzodiazepine compounds of formula I may be prepared byreacting a 2-nitrobenzoyl chloride of formula III with an amino acidester of formula IV wherein R₁₄ is C₁ -C₄ alkyl in the presence of abase to form a 2-nitrohippuric acid ester of formula V. Reduction of thenitro group of the formula V compound followed by in situ cyclization ofthe resultant 2-aminohippuric acid ester of formula Va affords thedesired compound. The reaction scheme is shown in Flow Diagram I.##STR4##

Advantageously, benzodiazepine compounds of formula II may be preparedfrom benzodiazepine compounds of formula I as shown in Flow Diagram II.##STR5##

Alternatively, the benzodiazepine compounds of formulas I and II may beprepared according to conventional methods; see, for example, U.S. Pat.Nos. 3,681,341, 3,947,408, 3,985,732, 4,031,079, 4,185,016, 4,316,839,4,352,815, 4,352,817 and 4,772,599; W. B. Wright, Jr., et al, Journal ofMedicinal Chemistry, 21, pp. 1087-1089 (1978); P. J. McCloskey and A. G.Schultz, Journal of Organic Chemistry, 53, pp. 1380-1383 (1988); T. T.Tita and M. J. Kornet, Journal of Heterocyclic Chem-istry, 24, pp.409-413 (1987); M. Mori, et al, Tetra-hedron, 42, pp. 3793-3806 (1986);T. Nagasaka, et al, Tetrahedron Letters, 30, pp. 1871-1872 (1989); A. G.Schultz, et al, Journal of the American Chemical Society, 109, pp.6493-6502 (1987); E. Wolf and H. Kohl, Liebigs Ann. Chem., pp. 1245-1251(1975); A. Kamal, Journal of Organic Chemistry, 56, pp. 2237-2240(1991); R. Singh, et al, Indian Journal of Chemistry, 20B, pp. 129-131(1981); and A. E. Azzouny, et al, Pharmazie, 32, pp. 318-323 (1977).

Unexpectedly, it has been found that the benzodiazepine compounds offormulas I and II are effective herbicidal agents useful for the controlof a wide variety of undesirable plant species. Those compounds areeffective for controlling weeds native to both dry land and wet landareas, especially when applied preemergence to the locus in which weedcontrol is desired. The compounds are also useful as aquatic herbicidesand are effective in controlling the above-said plants when applied tothe foliage thereof or to the soil, water, or other medium containingseeds or other propagating organs thereof, such as stolons, tubers orrhizomes, at rates of from about 0.10 kg/ha to 10.0 kg/ha.

Advantageously, the benzodiazepine compounds of formulas I and II,especially7-chloro-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione and7-chloro-1,2,3,11a-tetrahydro-3,3-dimethyl-5H-pyrrolo[2,1-c][1,4]-benzodiazepine-5,11(10H)-dione,are useful for the selective control of undesirable plant species in thepresence of cereal crops such as corn, barley, wheat, oat, rye and rice.The compounds are particularly suitable for the selective control ofundesirable plant species in the presence of corn. The compounds may beapplied to the cereal crops and undesirable plant species or to thesoil, water, or other medium containing seeds or other propagatingorgans of the undesirable plant species at rates of from about 0.10kg/ha to 2.5 kg/ha.

While the herbicidal agents of this invention are effective forcontrolling undesirable plant species when employed alone, they may alsobe used in combination with other biological chemicals, including otherherbicides.

The benzodiazepine compounds of formulas I and II may be applied in theform of a solid or liquid herbicidal composition, comprising aherbicidally effective amount of the formula I or formula II compounddispersed or dissolved in an agronomically acceptable solid or liquidcarrier. The formulations may be applied as preemergence orpostemergence treatments.

Advantageously, the herbicidal agents of the present invention may beformulated as emulsifiable concentrates, wettable powders, granularformulations, flowable concentrates and the like.

In order to facilitate a further understanding of the invention, thefollowing examples are presented primarily for the purpose ofillustrating more specific details thereof. The invention should not bedeemed limited thereby except as defined in the claims.

EXAMPLE 1 Preemergence herbicidal evaluation of test compounds

The preemergence herbicidal activity of the test compounds of thepresent invention is exemplified by the following tests in which theseeds of a variety of monocotyledonous and dicotyledonous plants areseparately mixed with potting soil and planted on top of approximatelyone inch of soil in separate pint cups. After planting, the cups aresprayed with the selected aqueous acetone solution containing testcompound in sufficient quantity to provide the equivalent of about 0.5to 10.0 kg per hectare of test compound per cup. The treated cups arethen placed on greenhouse benches, watered and cared for in accordancewith standard greenhouse procedures. At four to five weeks aftertreatment, the tests are terminated and each cup is examined and ratedaccording to the rating system set forth below. Data obtained arereported in Table I below. Where more than one test is involved for agiven compound, the data are averaged.

Plant species employed in these evaluations are reported by headerabbreviation, common name and scientific name.

Compounds employed in this preemergence herbicidal evaluation and in thepostemergence evaluation in the following example are given a compoundnumber and identified by name. Data in Table I are reported by compoundnumber.

Herbicide Rating Scale

Results of herbicide evaluation are expressed on a rating scale (0-9).The scale is based upon a visual observation of plant stand, vigor,malformation, size, chlorosis and overall plant appearance as comparedwith a control.

    ______________________________________                                                                  % Control                                           Rating Meaning            Compared to Check                                   ______________________________________                                        9      Complete Kill      100                                                 8      Approaching Complete Kill                                                                        91-99                                               7      Good Herbicidal Effect                                                                           80-90                                               6      Herbicidal Effect  65-79                                               5      Definite Injury    45-64                                               4      Injury             30-44                                               3      Moderate Effect    16-29                                               2      Slight Effect       6-15                                               1      Trace Effect       1-5                                                 0      No Effect           0                                                  --     No Evaluation                                                          ______________________________________                                    

    ______________________________________                                        PLANT SPECIES EMPLOYED IN HERBICIDAL                                          EVALUATIONS                                                                   Header                                                                        Abb.    Common Name   Scientific Name                                         ______________________________________                                        ABUTH   VELVETLEAF    ABUTILON THEOPHRASTI,                                                         MEDIC.                                                  AMBEL   RAGWEED,      AMBROSIA ARTEMISII                                              COMMON        FOLIA, L.                                               IPOSS   MORNING-      IPOMOEA SPP.                                                    GLORY SPP.                                                            SINAR   MUSTARD, WILD BRASSICA KABER, (DC)                                                          L. C. WHEELR                                            SOLNI   NIGHTSHADE,   SOLANUM NIGRUM, L.                                              BLACK                                                                 AVEFA   OAT, WILD     AVENA FATUA, L.                                         DIGSA   CRABGRASS,    DIGITARIA SANGUINALIS,                                          (HAIRY) L     (L) SCOP                                                SETVI   FOXTAIL,      SETARIA VIRIDIS,                                                GREEN         (L) BEAUV                                               GLXMAW  SOYBEAN,      GLYCINE MAX(L)MERR.                                             WILLIAMS      CV.WILLIAMS                                             GOSHI   COTTON        GOSSYPIUM HIRSUTUM, L.                                  ORYSAT  RICE,         ORYSA SATIVA, L.                                                TEBONNET      TEBONNET                                                TRZASK  WHEAT, SPRING,                                                                              TRICICUM AESTIVUM,                                              KATEP         KATEPWA                                                 ZEAMX   CORN, FIELD   ZEA MAYS L.                                                                   (SAMMEL-                                                                      BEZEICHNUNG)                                            ______________________________________                                    

    ______________________________________                                        COMPOUNDS EVALUATED AS HERBICIDAL AGENTS                                      Compound                                                                      Number                                                                        ______________________________________                                        1          1,2,3,11a-Tetrahydro-3-methyl-5H-pyrrolo[2,1-                                 c][1,4]benzodiazepine-5,11(10H)-dione                              2          7-Chloro-1,2,3,11a-tetrahydro-3,10-dimethyl-                                  5H-pyrrolo[2,1-c][1,4]benzodiazepine-                                         5,11(10H)-dione                                                    3          cis-1,2,3,11a-Tetrahydro-3,10-dimethyl-5H-                                    pyrrolo[2,1-c][1,4][benzodiazepine-5,11(10H)-                                 dione                                                              4          1,2,3,11a-Tetrahydro-3,7-dimethyl-5H-pyrrolo-                                 [2,1-c][1,4]benzodiazepine-5,11(10H)-dione                         5          7-Chloro-1,2,3,11a-tetrahydro-3-methyl-5H-                                    pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-                                  dione                                                              6          7-Chloro-1,2,3,11a-tetrahydro-2,10-dimethyl-                                  5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-                                    (10H)-dione                                                        7          7-Chloro-1,2,3,11a-tetrahydro-3-methyl-11-                                    thio-5H-pyrrolo[2,1-c][1,4]benzodiazepine-                                    5,11(10H)-dione                                                    8          1,2,3,11a-Tetrahydro-3-methyl-11-thio-5H-                                     pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-                                  dione                                                              9          1,2,3,11a-Tetrahydro-7-methoxy-3-methyl-5H-                                   pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-                                  dione                                                              10         cis-7-Chloro-1,2,3,11a-tetrahydro-3,9-                                        dimethyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine-                                5,11(10H)-dione                                                    11         1,2,3,11a-Tetrahydro-7-methoxy-3,10-dimethyl-                                 5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-                                    (10H)-dione                                                        12         trans-7-Chloro-1,2,3,11a-tetrahydro-3,10-                                     dimethyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine-                                5,11(10H)-dione                                                    13         1,2,3,11a-Tetrahydro-3,3-dimethyl-5H-pyrrolo-                                 [2,1-c][1,4]benzodiazepine-5,11(10H)-dione                         14         7-Chloro-1,2,3,11a-tetrahydro-3,3-dimethyl-5H-                                pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-                                  dione                                                              15         7-Chloro-3,4-dihydro-4-methyl-1H-1,4-benzo-                                   diazepine-2,5-dione                                                16         7-Chloro-3,4-dihydro-4-isopropyl-3-methyl-1H-                                 1,4-benzodiazepine-2,5-dione                                       17         1,2,3,11aα-Tetrahydro-3β,9-dimethyl-5H-                            pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-                                  dione                                                              18         7-Chloro-1,2,3,11a-tetrahydro-2,3,3-trimethyl-                                5H-pyrrolo[2,1-c][1,4]benzodiazepine-                                         5,11(10H)-dione                                                    19         7-Chloro-1,2,3,11a-tetrahydro-10-hydroxy-                                     2,3,3-trimethyl-5H-pyrrolo[2,1-c][1,4]-                                       benzodiazepine-5,11(10H)-dione                                     20         1,2,3,11a-Tetrahydro-2,3,3-trimethyl-5H-                                      pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-                                  dione                                                              21         7-Chloro-4-tert-butyl-3,4-dihydro-1H-1,4-                                     benzodiazepine-2,5-dione                                           22         4-Tert-butyl-3,4-dihydro-1H-1,4-benzo-                                        diazepine-2,5-dione                                                23         7-Chloro-3,4-dihydro-4-isopropyl-1H-1,4-                                      benzodiazepine-2,5-dione                                           24         1,2,3,11a-Tetrahydro-3,3,9-trimethyl-5H-                                      pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-                                  dione                                                              25         7-Chloro-1,2,3,11a-tetrahydro-10-hydroxy-3,3-                                 dimethyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine-                                5,11(10H)-dione                                                    26         4-Tert-butyl-3,4-dihydro-9-methyl-1H-1,4-                                     benzodiazepine-2,5-dione                                           27         4-Tert-butyl-3,4-dihydro-7-methyl-1H-1,4-                                     benzodiazepine-2,5-dione                                           28         4-Tert-butyl-3,4-dihydro-7-methoxy-1H-1,4-                                    benzodiazepine-2,5-dione                                           29         7-Chloro-3,4-dihydro-4-(2,2-dimethylpropyl)-                                  1H-1,4-benzodiazepine-2,5-dione                                    30         7-Chloro-3,4-dihydro-4-isobutyl-1H-1,4-                                       benzodiazepine-2,5-dione                                           31         7-Chloro-4-cyclohexyl-3,4-dihydro-1H-1,4-                                     benzodiazepine-2,5-dione                                           32         4-Cyclopentyl-7-chloro-3,4-dihydro-1H-1,4-                                    benzodiazepine-2,5-dione                                           33         1,2,3,11a-Tetrahydro-7-methoxy-3,3-dimethyl-                                  5H-pyrrolo[2,1-c][1,4]benzodiazepine-                                         5,11(10H)-dione                                                    34         1,2,3,11a-Tetrahydro-3,3,7-trimethyl-5H-                                      pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-                                  dione                                                              35         7-Chloro-4-cyclobutyl-3,4-dihydro-1H-1,4-                                     benzodiazepine-2,5-dione                                           36         7-Chloro-3,4-dihydro-4-phenyl-1H-1,4-benzo-                                   diazepine-2,5-dione                                                37         7-Chloro-3,4-dihydro-4-(1,1-dimethylpropyl)-                                  1H-1,4-benzodiazepine-2,5-dione                                    38         7-Bromo-4-tert-butyl-3,4-dihydro-1H-1,4-                                      benzodiazepine-2,5-dione                                           39         4-Tert-butyl-3,4-dihydro-7,9-dimethyl-1H-1,4-                                 benzodiazepine-2,5-dione                                           40         4-Tert-butyl-3,4-dihydro-7-iodo-1H-1,4-                                       benzodiazepine-2,5-dione                                           41         4-Tert-butyl-7-ethynyl-3,4-dihydro-1H-1,4-                                    benzodiazepine-2,5-dione                                           42         4-Tert-butyl-7-chloro-3,4-dihydro-2-thio-1H-                                  1,4-benzodiazepine-2,5-dione                                       43         4-Tert-butyl-7-chloro-3,4-dihydro-2-methoxy-                                  5H-1,4-benzodiazepin-5-one                                         44         4-Tert-butyl-7-chloro-3,4-dihydro-9-methyl-1H-                                1,4-benzodiazepine-2,5-dione                                       45         7-Chloro-4-(o-chlorobenzyl)-3,4-dihydro-1H-                                   1,4-benzodiazepine-2,5-dione                                       ______________________________________                                    

    TABLE I       Preemergence Herbicidal Evaluations of Test Compounds Compound Rate               Number (kg/ha) ABUTH AMBEL IPOSS SINAR SOLNI AVEFA DIGSA SETVI     GLXMAW GOSHI ORYSAT TRZASK ZEAMX       1 4.0 9.0 7.0 9.0 9.0 -- 8.0 6.0 7.0 -- 8.0 -- -- 2.0  1.0 5.0 4.5 8.0     6.5 4.0 3.0 0.0 2.5 4.0 3.5 2.0 0.0 1.0 2 10.0 5.0 9.0 9.0 9.0 -- 1.0     2.0 2.0 -- -- -- -- --  4.0 1.0 9.0 7.0 8.0 -- -- 3.0 0.0 --0.0 ----0.0     3 10.0 3.0 6.0 3.0 6.0 --1.0 0.0 1.0 -- -- -- -- -- 4 1.0 9.0 6.0 9.0     8.5 7.0 6.5 8.0 8.5 8.0 2.0 2.0 6.0 2.0  0.5 6.0 2.5 5.0 7.0 7.0 3.0 5.0     3.5 4.0 0.0 0.0 0.0 0.0 5 1.0 9.0 9.0 9.0 9.0 --9.0 8.0 6.7 9.0 6.3 3.0     7.0 2.3  0.5 8.3 5.7 9.0 8.7 9.0 4.5 6.0 4.7 2.0 2.0 2.0 4.0 0.7 6 5.0     5.0 3.0 6.0 7.0 -- 3.0 6.0 1.0 ---------- 7 1.0 9.0 9.0 9.0 9.0 --0.0     8.0 6.0 --0.0 ----2.0  0.5 3.0 9.0 8.0 9.0 --0.0 5.0 1.0 --0.0 ----0.0 8     4.0 9.0 6.0 9.0 9.0 --8.0 8.0 6.0 --7.0 ----5.0  1.0 5.0 0.0 8.0 5.0     --1.0 0.0 0.0 --0.0 ----0.0 9 4.0 9.0 8.0 9.0 9.0 --2.0 7.0 6.0 --3.0     ----6.0  1.0 8.0 3.0 9.0 8.0 --0.0 3.0 2.0 --0.0 ------ 10 1.0 9.0 8.0     9.0 9.0 9.0 8.5 9.0 7.0 6.0 2.5 5.0 8.0 3.5  0.5 7.5 5.5 7.5 8.5 7.0 3.0     8.0 3.5 5.0 1.0 3.0 3.0 1.0 11 10.0 6.0 6.0 8.0 9.0 --1.0 2.0 1.0     ----------  12 10.0 3.0 6.0 6.0 7.0 --1.0 0.0 0.0 ---------- 14 1.0 8.5     8.7 8.8 9.0 9.0 7.9 --8.7 8.3 7.1 3.3 7.9 3.0  0.5 7.6 8.2 8.8 9.0 8.7     6.6 --7.1 6.7 4.4 2.8 5.9 1.8 15 10.0 8.0 0.0 6.0 7.0 --0.0 0.0 0.0------     ---- 16 4.0 9.0 8.0 9.0 9.0 --8.0 8.0 8.0 --6.0 ----6.0  1.0 4.7 2.7 6.0     6.3 3.0 1.3 1.0 1.3 4.5 1.7 0.5 1.0 0.0 17 1.0 2.0 2.0 6.0 9.0 4.0 0.0     --4.0 1.0 2.0 0.0 0.0 0.0 18 1.0 4.0 5.0 8.0 9.0 8.0 2.0 --2.0 2.0 1.0     0.0 1.0 0.0  0.5 2.0 2.0 1.0 9.0 8.0 1.0 --1.0 1.0 1.0 0.0 1.0 0.0 19     1.0 2.0 2.0 0.0 9.0 9.0 0.0 --2.0 3.0 --0.0 0.0 0.0 20 0.5 9.0 4.0 9.0     9.0 7.0 0.0 --4.0 5.0 2.0 2.0 0.0 0.0 21 1.0 9.0 8.8 9.0 9.0 9.0 7.8     --8.8 8.3 9.0 4.9 7.4 4.5  0.5 9.0 8.7 8.9 9.0 8.9 7.2 --8.4 7.9 8.7 3.9     7.0 3.0 22 1.0 8.0 9.0 9.0 9.0 9.0 8.0 --7.0 7.0 9.0 3.0 7.0 2.0  0.5     6.0 9.0 9.0 7.0 3.0 4.0 --1.0 7.0 5.0 2.0 3.0 0.0 23 1.0 9.0 8.0 9.0 8.0     6.0 3.0 --0.0 6.0 9.0 2.0 1.0 0.0 24 1.0 7.0 7.0 9.0 9.0 2.0 4.0 --1.0     8.0 7.0 2.0 2.0 0.0 25 1.0 2.0 8.0 4.0 9.0 9.0 2.0 --0.0 2.0 2.0 2.0 2.0     0.0 26 1.0 9.0 8.0 9.0 9.0 8.0 8.0 --6.0 9.0 9.0 4.0 8.0 4.0  0.5 9.0     6.0 9.0 8.0 8.0 7.0 --6.0 7.0 7.0 3.0 7.0 1.0 27 1.0 8.5 8.0 8.0 9.0 8.5     8.5 -- 9.0 7.5 9.0 4.5 5.0 3.5  0.5 8.5 8.0 9.0 9.0 8.5 8.0 --7.0 7.5     8.5 3.0 5.0 2.0 28 1.0 8.0 6.0 4.0 9.0 7.0 1.0 -- 0.0 2.0 7.0 0.0 0.0     0.0 29 1.0 9.0 8.5 9.0 8.5 9.0 6.0 9.0 3.5 6.0 9.0 6.0 6.0 4.5  0.5 5.0     5.5 9.0 8.0 9.0 4.0 9.0 1.0 4.5 9.0 3.5 2.0 3.0 30 1.0 1.0 0.0 0.0 0.0     0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 31 1.0 6.0 7.0 4.0 9.0 7.0 3.0 --     6.0 3.0 6.0 3.0 2.0 2.0 32 4.0 9.0 8.0 9.0 9.0 -- 8.0 --8.0 6.0 ------6.0       1.0 9.0 2.0 6.0 9.0 9.0 2.0 --4.0 0.0 2.0 4.0 0.0 0.0 33 0.75 9.0 7.0     4.0 9.0 8.0 2.0 -- 4.0 2.0 4.0 2.0 0.0 0.0 34 1.0 9.0 9.0 9.0 9.0 9.0     7.0 --9.0 7.0 6.0 4.0 4.0 3.0  0.5 9.0 6.0 9.0 9.0 9.0 3.0 --4.0 7.0 4.0     3.0 1.0 1.0 35 1.0 9.0 8.0 2.0 9.0 8.0 4.0 --7.0 3.0  8.0 3.0 4.0 0.0     0.5 8.0 8.0 1.0 9.0 8.0 2.0 --2.0 1.0 4.0 2.0 2.0 0.0 36 1.0 6.0 6.0 8.0     9.0 8.0 4.0 --6.0 6.0 7.0 4.0 0.0 0.0  0.5 2.0 4.0 7.0 9.0 8.0 2.0 --4.0     3.0 4.0 1.0 0.0 0.0 37 1.0 9.0 8.0 4.0 9.0 8.0 4.0 --6.0 6.0 7.0 3.0 6.0     2.0  0.5 7.0 6.0 4.0 9.0 7.0 2.0 --3.0 6.0 4.0 2.0 4.0 1.0 38 1.0 9.0     9.0 9.0 9.0 9.0 9.0 --9.0 9.0 9.0 7.0 9.0 6.0  0.5 8.0 8.0 9.0 9.0 9.0     7.0 --7.0 9.0 9.0 4.0 7.0 4.0 39 1.0 9.0 8.0 9.0 9.0 9.0 9.0 --9.0 9.0     9.0 7.0 9.0 7.0  0.5 7.0 7.0 9.0 9.0 9.0 9.0 --9.0 9.0 9.0 7.0 7.0 3.0     40 1.0 0.0 0.0 0.0 --4.0 0.0 --0.0 0.0 0.0 0.0 0.0 0.0 41 1.0 8.0 6.0     8.0 9.0 8.0 4.0 --9.0 7.0 9.0 3.0 2.0 0.0  0.5 4.0 4.0 8.0 9.0 6.0 2.0     --2.0 6.0 2.0 2.0 0.0 42 1.0 9.0 8.0 8.0 9.0 9.0 7.0 --9.0 7.0 9.0 6.0     7.0 5.0  0.5 9.0 8.0 8.0 9.0 9.0 6.0 --9.0 6.0 9.0 6.0 7.0 4.0 43 1.0     2.0 7.0 9.0 9.0 7.0 5.0 --6.0 3.0 2.0 3.0 3.0 2.0 44 1.0 4.0 7.0 6.0 9.0     7.0 4.0 --6.0 3.0 5.0 2.0 2.0 1.0 45 1.0 0.0 0.0 0.0 9.0 9.0 0.0 -- 0.0     0.0 0.0 0.0 0.0 0.0

EXAMPLE 2 Postemergence herbicidal evaluation of test compounds

The postemergence herbicidal activity of the compounds of the presentinvention is demonstrated by the following tests, wherein a variety ofdicotyledonous and monocotyledonous plants are treated with testcompounds, dispersed in aqueous acetone mixtures. In the tests, seedlingplants are grown in jiffy flats for about two weeks. The test compoundsare dispersed in 50/50 acetone/water mixtures containing 0.5% TWEEN®20,a polyoxyethylene sorbitan monolaurate surfactant of Atlas ChemicalIndustries, in sufficient quantities to provide the equivalent of about0.5 kg to 10.0 kg per hectare of test compound when applied to theplants through a spray nozzle operating at 40 psi for a predeterminedtime. After spraying, the plants are placed on greenhouse benches andare cared for in the usual manner, commensurate with conventionalgreenhouse practices. From four to five weeks after treatment, theseedling plants are examined and rated according to the rating systemprovided in Example 1.

The data obtained are reported in Table II below. The compoundsevaluated are reported by compound number given in Example 1.

    TABLE II       Postemergence Herbicidal Evaluations of Test Compounds Compound Rate                Number (kg/ha) ABUTH AMBEL IPOSS SINAR SOLNI AVEFA DIGSA     SETVI GLXMAW GOSHI ORYSAT TRZASK ZEAMX       1 10.0 3.0 0.0 3.0 5.0 -- 0.0 0.0 0.0 -- -- -- -- --  1.0 0.0 0.0 0.0     2.0 4.0 0.0 -- 0.0 4.0 4.0 0.0 0.0 0.0 2 10.0 1.0 0.0 2.0 2.0 --0.0 0.0     0.0 ---------- 3 10.0 1.0 4.0 0.0 1.0 --0.0 0.0 0.0 ---------- 4 4.0 9.0     9.0 9.0 9.0 ----0.0 2.0 --5.0 ----3.0  1.0 6.5 4.5 4.5 7.5 2.0 0.0 0.0     0.0 3.0 4.0 0.0 0.0 0.5 5 1.0 4.5 4.5 6.8 6.5 8.0 2.5 1.0 3.0 7.0 8.5     2.0 1.0 0.8  0.5 4.5 1.3 4.8 6.0 7.0 1.0 0.7 2.3 6.0 6.8 0.0 1.0 0.5 6     5.0 0.0 0.0 2.0 2.0 --0.0 0.0 0.0 ---------- 7 10.0 1.0 1.0 5.0 2.0     --0.0 0.0 0.0---------- 8 10.0 3.0 0.0 3.0 2.0 --0.0 0.0 0.0---------- 9     10.0 9.0 7.0 8.0 9.0 --5.0 3.0 6.0 ----------  4.0 7.0 6.0 9.0 9.0     ----0.0 1.0 --6.0 ----1.0 10 4.0 7.0 5.0 9.0 9.0 ----2.0 3.0 --9.0     ----0.0  1.0 5.0 1.0 5.0 3.5 4.0 1.0 0.0 1.0 4.0 6.5 1.0 1.0 0.0 11 10.0     1.0 0.0 2.0 2.0 --0.0 0.0 0.0---------- 12 10.0 2.0 0.0 1.0 2.0 --0.0     0.0 0.0 ---------- 13 4.0 4.0 2.0 7.0 2.0 4.0 2.0 --6.0 6.0 5.0 2.0 1.0     3.0 14 1.0 7.7 7.8 8.4 9.0 9.0 4.3 5.3 5.6 7.9 8.1 2.1 2.9 1.6  0.5 6.4     7.0 7.0 8.8 8.8 2.9 2.3 3.0 6.9 8.3 1.0 1.7 1.0 15 10.0 1.0 0.0 2.0 3.0     --0.0 0.0 0.0 ---------- 16 10.0 3.0 7.0 --9.0 --7.0 3.0 3.0----------     17 1.0 7.0 2.0 4.0 4.0 4.0 0.0 --0.0 7.0 7.0 0.0 0.0 0.0 18 1.0 9.0 6.0     8.0 9.0 9.0 1.0 --8.0 7.0 7.0 0.0 2.0 0.0  0.5 9.0 4.0 8.0 9.0 9.0 0.0     --5.0 1.0 4.0 0.0 1.0 0.0 19 1.0 4.0 2.0 9.0 8.0 9.0 1.0 --2.0 7.0 7.0     1.0 0.0 0.0 20 1.0 4.0 9.0 9.0 8.0 9.0 2.0 --9.0 7.0 7.0 0.0 2.0 2.0 21     1.0 9.0 8.3 8.5 9.0 9.0 5.5 --7.8 8.4 9.0 2.4 5.0 3.9  0.5 9.0 7.4 7.9     9.0 9.0 4.0 --6.0 8.0 8.8 2.2 3.2 3.0 22 1.0 9.0 4.0 7.0 9.0 9.0 0.0     --0.0 7.0 9.0 3.0 3.0 1.0  0.5 8.0 2.0 4.0 9.0 9.0 0.0 --0.0 5.0 7.0 1.0     1.0 0.0 23 1.0 6.0 0.0 6.0 9.0 4.0 0.0 --0.0 3.0 2.0 0.0 0.0 0.0  24 1.0     4.0 0.0 2.0 4.0 0.0 0.0 --0.0 2.0 2.0 0.0 0.0 0.0 25 1.0 0.0 0.0 0.0 9.0     9.0 0.0 --0.0 2.0 3.0 0.0 0.0 0.0 26 1.0 9.0 6.0 8.0 9.0 9.0 7.0 --4.0     6.0 6.0 4.0 4.0 1.0  0.5 9.0 1.0 4.0 6.0 4.0 2.0 --1.0 3.0 6.0 2.0 3.0     0.0 27 1.0 9.0 8.5 8.5 9.0 9.0 6.5 --7.5 8.0 8.5 5.0 4.0 1.5  0.5 8.0     7.0 8.0 9.0 9.0 3.5 2.0 6.0 8.0 2.5 3.0 1.0 28 1.0 8.0 6.0 4.0 9.0 7.0     1.0 --0.0 2.0 7.0 0.0 0.0 0.0 29 1.0 9.0 8.0 9.0 8.0 9.0 2.0 --0.0 3.0     9.0 4.0 6.0 2.0  0.5 4.0 2.0 9.0 7.0 9.0 2.0 --0.0 1.0 9.0 1.0 2.0 1.0     30 1.0 9.0 4.0 8.0 9.0 9.0 0.0 --0.0 4.0 9.0 0.0 2.0 0.0  0.5 9.0 2.0     7.0 9.0 8.0 0.0 --0.0 4.0 8.0 0.0 1.0 0.0 31 1.0 9.0 0.0 6.0 9.0 9.0 0.0     --0.0 2.0 6.0 0.0 0.0 0.0 32 4.0 9.0 7.0 9.0 9.0 --0.0 --9.0 2.0     ------2.0  1.0 4.0 2.0 4.0 9.0 7.0 0.0 --0.0 0.0 6.0 0.0 0.0 0.0 33 0.75     4.0 2.0 6.0 9.0 6.0 0.0 --0.0 4.0 6.0 0.0 2.0 0.0 34 1.0 9.0 8.0 9.0 9.0     9.0 0.0 --6.0 8.0 9.0 2.0 2.0 1.0  0.5 8.0 7.0 9.0 9.0 8.0 0.0 --2.0 6.0     6.0 1.0 2.0 0.0 35 1.0 9.0 6.0 4.0 9.0 9.0 0.0 --0.0 4.0 6.0 1.0 2.0 0.0      0.5 9.0 4.0 4.0 9.0 9.0 0.0 --0.0 4.0 5.0 0.0 2.0 0.0 36 1.0 9.0 4.0     9.0 9.0 8.0 4.0 --2.0 4.0 9.0 2.0 2.0 2.0  0.5 7.0 3.0 7.0 9.0 6.0 2.0     --1.0 3.0 9.0 2.0 2.0 1.0 37 1.0 9.0 6.0 6.0 9.0 6.0 0.0 --2.0 6.0 8.0     0.0 0.0 0.0  0.5 6.0 2.0 2.0 6.0 4.0 0.0 --1.0 4.0 8.0 0.0 0.0 0.0 38     1.0 9.0 9.0 8.0 9.0 9.0 3.0 --9.0 9.0 9.0 2.0 2.0 2.0  0.5 8.0 4.0 7.0     9.0 9.0 2.0 --4.0 6.0 8.0 2.0 2.0 2.0 39 1.0 9.0 7.0 9.0 9.0 9.0 4.0     --9.0 8.0 9.0 3.0 2.0 2.0  0.5 6.0 6.0 8.0 9.0 9.0 3.0 --4.0 7.0 9.0 2.0     2.0 2.0 40 1.0 7.0 4.0 0.0 9.0 9.0 0.0 --4.0 5.0 7.0 0.0 0.0 0.0 41 1.0     0.0 2.0 8.0 6.0 9.0 0.0 --0.0 6.0 3.0 0.0 2.0 0.0 42 1.0 5.0 9.0 6.0 9.0     --4.0 --9.0 6.0 9.0 4.0 4.0 2.0  0.5 3.0 7.0 8.0 8.0 2.0 5.0 6.0 6.0 0.0     2.0 0.0 43 1.0 5.0 7.0 5.0 7.0 --2.0 --9.0 9.0 5.0 2.0 3.0 1.0 44 1.0     2.0 3.0 4.0 6.0 7.0 0.0 --2.0 2.0 2.0 0.0 0.0 0.0 45 1.0 7.0 9.0 3.0 9.0     9.0 0.0 --0.0 3.0 6.0 0.0 2.0 2.0  0.5 2.0 8.0 2.0 9.0 8.0 0.0 --0.0 3.0     6.0 0.0 2.0 2.0

EXAMPLE 3 Preparation of 5-Chloro-2-nitrobenzoyl chloride ##STR6##

A mixture of thionyl chloride (7.25 mL, 99.5 mmol) andN,N-dimethylformamide is added to a mixture of 5-chloro-2-nitrobenzoicacid in toluene. The reaction mixture is heated to and held at 80° C.for 16 hours, cooled to room temperature, concentrated in vacuo, dilutedwith toluene, concentrated in vacuo and diluted with toluene to obtainthe title product as a 1 molar solution in toluene.

Using essentially the same procedure, but using the appropriatelysubstituted 2-nitrobenzoic acid, the following compounds are obtained:

    ______________________________________                                         ##STR7##                                                                     X              X.sub.1      X.sub.3                                           ______________________________________                                        H              H            H                                                 H              H            CH.sub.3                                          H              CH.sub.3     H                                                 CH.sub.3       H            H                                                 H              OCH.sub.3    H                                                 H              CH.sub.3     CH.sub.3                                          ______________________________________                                    

EXAMPLE 4 Preparation of Methyl N-tert-butylglycinate

    (CH.sub.3).sub.3 CNH.sub.2 +BrCH.sub.2 CO.sub.2 CH.sub.3 →(CH.sub.3).sub.3 CNHCH.sub.2 CO.sub.2 CH.sub.3

Methyl bromoacetate (7.1 mL, 75 mmol) is added dropwise totert-butylamine (31.5 mL, 300 mmol) at 0° C. The reaction mixture isdiluted with ether, warmed to room temperature and filtered. Thefiltrate is concentrated in vacuo to obtain the title product as a clearliquid (10.52 g) which is identified by ¹ H and ¹³ CNMR spectralanalyses.

Using essentially the same procedure, but using the appropriatelysubstituted amine and methyl bromoacetate, the following compounds areobtained:

    ______________________________________                                         ##STR8##                                                                     R                      R.sub.1                                                ______________________________________                                        CH(CH.sub.3).sub.2     CH.sub.3                                               CH.sub.2 C(CH.sub.3).sub.3                                                                           H                                                       ##STR9##              H                                                       ##STR10##             H                                                      CH(CH.sub.3).sub.2     H                                                      CH.sub.2 CH(CH.sub.3).sub.2                                                                          H                                                       ##STR11##             H                                                       ##STR12##             H                                                      C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                                                                  H                                                      CH.sub.2 C(CH.sub.3).sub.3                                                                           CH.sub.3                                               ______________________________________                                    

EXAMPLE 5 Preparation of Methyl β-tert-butyl-5-chloro-2-nitrohippurate##STR13##

A 1 molar solution of 5-chloro-2-nitrobenzoyl chloride in toluene (20mL, 20 mmol) is added to a mixture of methyl N-tert-butylglycinate (2.17g, 15 mmol)and triethylamine (5.2 g, 37.5 mmol) in tetrahydrofuran at 0°C. The reaction mixture is stirred overnight at room temperature andpoured into an ethyl acetate/water mixture. Tetrahydrofuran andmethylene chloride are added to the mixture and the phases areseparated. The organic phase is washed sequentially with 10%hydrochloric acid, saturated sodium hydrogen carbonate solution andbrine, dried over anhydrous sodium sulfate and concentrated in vacuo toobtain an off-white solid. The solid is recrystallized from anethanol/water mixture to give the title product as white needles (3.25g, mp 155°-156° C.).

Using essentially the same procedure, but using the appropriatelysubstituted 2-nitrobenzoyl chloride and methyl glycinate, the followingcompounds are obtained:

    ______________________________________                                         ##STR14##                                                                    X.sub.1    X.sub.3  R               R.sub.1                                   ______________________________________                                        Cl         H        CH(CH.sub.3).sub.2                                                                            CH.sub.3                                  H          H        C(CH.sub.3).sub.3                                                                             H                                         H          CH.sub.3 C(CH.sub.3).sub.3                                                                             H                                         CH.sub.3   H        C(CH.sub.3).sub.3                                                                             H                                         Cl         H        CH.sub.2 C(CH.sub.3).sub.3                                                                    H                                         Cl         H                                                                                       ##STR15##      H                                         Cl         H                                                                                       ##STR16##      H                                         Cl         H        CH(CH.sub.3).sub.2                                                                            H                                         OCH.sub.3  H        C(CH.sub.3).sub.3                                                                             H                                         Cl         H        CH.sub.2 CH(CH.sub.3).sub.2                                                                   H                                         Cl         H                                                                                       ##STR17##      H                                         Cl         H                                                                                       ##STR18##      H                                         Cl         H        C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                                                           H                                         CH.sub.3   CH.sub.3 C(CH.sub.3).sub.3                                                                             H                                         Cl         H        CH.sub.2 C(CH.sub.3).sub.3                                                                    CH.sub.3                                  ______________________________________                                    

EXAMPLE 6 Preparation of7-Chloro-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione##STR19##

A mixture of methyl β-tert-butyl-5-chloro-2-nitrohippurate (2.45 g, 7.5mmol) and 5% platinum on carbon (0.98 g, 40 wt % of 5% Pt/C) in a 1:1tetrahydrofuran/ethanol solution is shaken in a Parr Hydrogenator undera hydrogen pressure of 50 psi until 18.5 psi is taken up. The reactionmixture is filtered and the filtrate is concentrated in vacuo to give anoil. The oil is heated at reflux for 26 hours, cooled to roomtemperature and concentrated in vacuo to obtain an amber oil. The oil isdissolved in ethyl acetate and the resultant solution is concentrated invacuo to form a solid. The solid is recrystallized from ethylacetate/hexanes to give the title product as white needles (1.21 g, mp177°-178° C.).

Using essentially the same procedure, but using the appropriatelysubstituted methyl 2-nitrohippurate, the following compounds areobtained:

    ______________________________________                                         ##STR20##                                                                    X.sub.1                                                                              X.sub.3  R             R.sub.1                                                                             mp °C.                             ______________________________________                                        Cl     H        CH(CH.sub.3).sub.2                                                                          CH.sub.3                                                                            228-230                                   H      H        C(CH.sub.3).sub.3                                                                           H     183-184                                   H      CH.sub.3 C(CH.sub.3).sub.3                                                                           H       169-171.5                               CH.sub.3                                                                             H        C(CH.sub.3).sub.3                                                                           H     156-157                                   Cl     H        CH.sub.2 C(CH.sub.3).sub.3                                                                  H     195-196                                   Cl     H                                                                                       ##STR21##    H     205-206                                   Cl     H                                                                                       ##STR22##    H     222-224                                   Cl     H        CH(CH.sub.3).sub.2                                                                          H     203-205                                   OCH.sub.3                                                                            H        C(CH.sub.3).sub.3                                                                           H     196-198                                   Cl     H        CH.sub.2 CH(CH.sub.3).sub.2                                                                 H     203.5-205.5                               Cl     H                                                                                       ##STR23##    H     238-239                                   Cl     H                                                                                       ##STR24##    H     215.5-217                                 Cl     H        C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                                                         H     149-151                                   CH.sub.3                                                                             CH.sub.3 C(CH.sub.3).sub.3                                                                           H     186-187                                   Cl     H        CH.sub.2 C(CH.sub.3).sub.3                                                                  CH.sub.3                                                                            153-154                                   ______________________________________                                    

EXAMPLE 7 Preparation of7-Bromo-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione##STR25##

Bromine (1.72 g, 10.8 mmol) is added to a mixture of4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (1.0 g, 4.3mmol) and sodium acetate (0.39 g, 4.8 mmol) in acetic acid. The reactionmixture is stirred at room temperature for 29 hours, concentrated invacuo, diluted with ethyl acetate, washed sequentially with 0.1N sodiumhydroxide solution and brine, dried over anhydrous sodium sulfate andconcentrated in vacuo to give a residue. Chromatography of the residueusing silica gel and 20% to 25% ethyl acetate in hexanes solutions givesthe title product as a white solid (0.86 g, mp 205°-208° C.).

EXAMPLE 8 Preparation of4-Tert-butyl-3,4-dihydro-7-iodo-1H-1,4-benzodiazepine-2,5-dione##STR26##

Bis(trifluoroacetoxy)phenyl iodine (2.05 g, 4.7 mmol) is added to asolution of 4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione(1.0 g, 4.3 mmol) and iodine (1.1 g, 4.3 mmol) in methylene chloride.The reaction mixture is stirred overnight at room temperature, dilutedwith ethyl acetate, washed sequentially with saturated sodium hydrogencarbonate solution, 1N sodium thiosulfate solution and brine, dried overanhydrous sodium sulfate and concentrated in vacuo to obtain a residue.Chromatography of the residue using silica gel and 20% to 25% ethylacetate in hexanes solutions gives the title product as a beige solid(0.9 g, mp 230°-232° C.).

EXAMPLE 9 Preparation of4-Tert-butyl-3,4-dihydro-7-[(trimethylsilyl)ethynyl]-1H-1,4-benzodiazepine-2,5-dione##STR27##

(Trimethylsilyl)acetylene (1.18 mL, 8.4 mmol), copper(I) iodide (0.05 g,0.28 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.1 g,0.14 mmol) are added sequentially to a degassed suspension of4-tert-butyl-3,4-dihydro-7-iodo-1H-1,4-benzodiazepine-2,5-dione (2.5 g,7.0 mmol) in triethylamine. The reaction mixture is stirred at roomtemperature for 5 hours and filtered. The filtrate is diluted with etherand concentrated in vacuo to obtain a solid. Chromatography of the solidusing silica gel and 15% to 20% ethyl acetate in hexanes solutions givesthe title product as a light brown solid (1.33 g, mp 243°-244° C.).

EXAMPLE 10 Preparation of4-Tert-butyl-7-ethynyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione##STR28##

1N Sodium hydroxide solution (3.4 mL) is added to a suspension of4-tert-butyl-3,4-dihydro-7-[(trimethylsilyl)ethynyl]-1H-1,4-benzodiazepine-2,5-dione(1.0 g, 3.0 mmol) in methanol. The reaction mixture is stirred at roomtemperature for 2 hours, concentrated in vacuo and extracted with ethylacetate. The combined organic extracts are washed with brine, dried overanhydrous sodium sulfate and concentrated in vacuo to give the titleproduct as a light brown solid (0.66 g, mp 216°-219° C.).

EXAMPLE 11 Preparation of4-Tert-butyl-7-chloro-3,4-dihydro-2-thio-1H-1,4-benzodiazepine-2,5-dione##STR29##

A mixture of7-chloro-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (0.5g, 1.9 mmol) and2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide(0.42 g, 1.0 mmol) in toluene is heated at reflux for 30 minutes,treated with additional2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide(0.42 g, 1.0 mmol), heated at reflux for 1 hour, cooled and concentratedin vacuo to obtain a residue. Flash column chromatography of the residueusing silica gel and 20% to 40% ethyl acetate in hexanes solutions givesthe title product as a yellow solid (0.34 g, mp 196°-197° C.).

EXAMPLE 12 Preparation of4-Tert-butyl-7-chloro-3,4-dihydro-2-methoxy-5H-1,4-benzodiazepin-5-one##STR30##

Methyl iodide (233 μL, 3.7 mmol) is added to a mixture of7-chloro-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (0.5g, 1.9 mmol) and potassium carbonate (1.04 g, 7.5 mmol) intetrahydrofuran. The reaction mixture is stirred at room temperature for16 hours, heated at reflux for 90 hours, filtered through diatomaceousearth and concentrated in vacuo to obtain a residue. Flash columnchromatography of the residue using silica gel and 33% to 50% ethylacetate in hexanes solutions gives the title product as a clear oil(0.63 g) which is identified by ¹ HNMR spectral analysis.

EXAMPLE 13 Preparation of9-chloro-4-tert-butyl-3,4-dihydro-7-methyl-1H-1,4-benzodiazepine-2,5-dione##STR31##

Chlorine gas (100 mL, 4.1 mmol) is added via syringe to a mixture of4-tert-butyl-3,4-dihydro-7-methyl-1H-1,4-benzodiazepine-2,5-dione (1.0g, 4.1 mmol) and a few grains of ferric chloride hexahydrate in aceticacid. The reaction mixture is stirred at room temperature overnight,poured into water and extracted with ethyl acetate. The combined organicextracts are washed sequentially with water, dilute sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate andconcentrated in vacuo to obtain a foam. Flash column chromatography ofthe foam using silica gel and a 20:1 methylene chloride/ethyl acetatesolution gives the title product as a white solid (0.5 g, mp 151°-152°C.).

What is claimed is:
 1. A method for controlling undesirable plantspecies which comprises applying to the foliage of said plants or to thesoil or water containing seeds or other propagating organs thereof, aherbicidally effective amount of a compound having the structuralformula ##STR32## wherein X is hydrogen, halogen, C₁ -C₄ haloalkyl, C₁-C₄ alkoxy, C₁ -C₄ haloalkoxy, C₂ -C₃ alkenyl, C₂ -C.sub. alkynyl, CO₂R₅, C(O)NR₆ R₇, S(O)_(m) R₈, C(O)R₉, or benzyl optionally substitutedwith one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl,C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups;X₁ is hydrogen, halogen,methyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₂ -C₅alkynyl, CO₂ R₅, C(O)NR₆ R₇, S(O)_(m) R₈, C(O)R₉, or benzyl optionallysubstituted with one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups; X₂ is hydrogen, C₁-C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₂ -C₃ alkenyl, C₂ -C₃alkynyl, CO₂ R₅, C(O)NR₆ R₇, S(O)_(m) R₈, C(O)R₉, or benzyl optionallysubstituted with one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups; X₃ is hydrogen, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy, C₂ -C₃ alkenyl, C₂ -C₃alkynyl, CO₂ R₅, C(O)NR₆ R₇, S(O)_(m) R₈, C(O)R₉, or benzyl optionallysubstituted with one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups; R₅ is hydrogen, C₁-C₄ alkyl, benzyl optionally substituted with one or more halogen,nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄haloalkoxy groups, or an alkali metal, alkaline earth metal, manganese,copper, zinc, cobalt, silver, nickel, ammonium or organic ammoniumcation; R₆ and R₇ are each independently C₁ -C₄ alkyl, benzyl optionallysubstituted with one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups, phenyl optionallysubstituted with one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups, or R₆ and R₇ aretaken together to form a ring in which R₆ R₇ is represented by--(CH₂)_(n) -- where n is an integer of 2, 3, 4 or 5; m is an integer of0, 1 or 2; R₈ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, NR₁₀ R₁₁,OR₁₂ or phenyl optionally substituted with one or more halogen, nitro,cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄haloalkoxy groups; R₁₀ and R₁₁ are each independently hydrogen, C₁ -C₄alkyl, benzyl optionally substituted with one or more halogen, nitro,cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄haloalkoxy groups, phenyl optionally substituted with one or morehalogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy orC₁ -C₄ haloalkoxy groups, or R₁₀ and R₁₁ are taken together to form aring in which R₁₀ R₁₁ is represented by --(CH₂)_(q) -- where q is aninteger of 2, 3, 4 or 5; R₁₂ is hydrogen or C₁ -C₄ alkyl; R₉ ishydrogen, C₁ -C₄ alkyl or phenyl optionally substituted with one or morehalogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy orC₁ -C₄ haloalkoxy groups; A, A₁ and W are each independently O or S withthe proviso that when A₁ is S then A is O; R is C₃ -C₆ cycloalkyl, C₂-C₅ alkenyl, C₂ -C₅ alkynyl, C₁ -C₅ alkyl optionally substituted withone CO₂ R₁₃ group, one phenyl group optionally substituted with one ormore halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy or C₁ -C₄ haloalkoxy groups, or one 5- or 6-membered heterocyclegroup containing one to three nitrogen atoms, one oxygen atom and/or onesulfur atom and two to five carbon atoms optionally substituted with oneor more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy or C₁ -C₄ haloalkoxy groups, phenyl optionally substituted withone or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁-C₄ alkoxy or C₁ -C₄ haloalkoxy groups with the proviso that thepara-position of the phenyl ring is not substituted, a 5- or 6-memberedheterocycle group containing one to three nitrogen atoms, one oxygenatom and/or one sulfur atom and two to five carbon atoms optionallysubstituted with one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups, or R may be takentogether with R₁ and the atoms to which they are attached to form a fivemembered saturated ring substituted with one to three C₁ -C₄ alkylgroups; R₁₃ is hydrogen, C₁ -C₄ alkyl, benzyl optionally substitutedwith one or more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl,C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups, or an alkali metal, alkalineearth metal, manganese, copper, zinc, cobalt, silver, nickel, ammoniumor organic ammonium cation; R₁ and R₂ are each independently hydrogen,methyl, ethyl, or R₁ may be taken together with R and the atoms to whichthey are attached to form a five membered saturated ring substitutedwith one to three C₁ -C₄ alkyl groups, and when taken together, R₁ andR₂ may form a ring in which R₁ R₂ is represented by --(CH₂)_(t) -- wheret is an integer of 2, 3, 4, 5 or 6 with the proviso that when R₁ ismethyl or ethyl then R₂ is hydrogen; R₃ is hydrogen, C₁ -C₄ alkyl orhydroxy with the proviso that when R₃ is hydroxy, X₂ is other than C₁-C₄ alkyl, and further with the proviso that when R₃ is C₁ -C₄ alkyl, X₁is other than hydrogen or methyl; and R₄ is C₁ -C₆ alkyl, C₃ -C₆cycloalkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkenyl, C₂ -C₆ alkynyl, benzyloptionally substituted with one or more halogen, nitro, cyano, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy groups, orphenyl optionally substituted with one halogen, nitro, cyano, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy group; andthe optical isomers and diastereomers thereof; and mixtures thereof. 2.The method according to claim 1 whereinX and X₂ are hydrogen; X₁ ishydrogen, halogen, methyl, C₁ -C₄ alkoxy or C₂ -C₃ alkynyl; X₃ ishydrogen or methyl; A is O; A₁ and W are each independently O or S; R isC₃ -C₆ cycloalkyl, C₁ -C₅ alkyl, phenyl optionally substituted with oneor more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy or C₁ -C₄ haloalkoxy groups with the proviso that thepara-position of the phenyl ring is not substituted, or R may be takentogether with R₁ and the atoms to which they are attached to form a fivemembered saturated ring substituted with one to three C₁ -C₄ alkylgroups; R₁ and R₂ are hydrogen or R₁ may be taken together with R andthe atoms to which they are attached to form a five membered saturatedring substituted with one to three C₁ -C₄ alkyl groups; R₃ is hydrogenor hydroxy; and R₄ is C₁ -C₆ alkyl, C₃ -C₆ cycloalkyl, C₁ -C₆ haloalkyl,C₂ -C₆ alkenyl, C₂ -C₆ alkynyl, benzyl optionally substituted with oneor more halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy or C₁ -C₄ haloalkoxy groups, or phenyl optionally substitutedwith one halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy or C₁ -C₄ haloalkoxy group.
 3. The method according to claim 2whereinX, X₂, X₃, R₂ and R₃ are hydrogen; X₁ is hydrogen, halogen ormethyl; A, A₁ and W are O; R is C₃ -C₆ cycloalkyl, C₁ -C₅ alkyl, or Rmay be taken together with R₁ and the atoms to which they are attachedto form a five membered saturated ring substituted with one to three C₁-C₄ alkyl groups; R₁ is hydrogen or R₁ may be taken together with R andthe atoms to which they are attached to form a five membered saturatedring substituted with one to three C₁ -C₄ alkyl groups; and R₄ is C₁ -C₆alkyl.
 4. The method according to claim 3 wherein the compound isselected from the group consistingof7-chloro-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione;7-chloro-1,2,3,11a-tetrahydro-3,3-dimethyl-5H-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11(10H)-dione;7-chloro-1,2,3,11a-tetrahydro-2,3,3-trimethyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione;4-tert-butyl-3,4-dihydro-7-methyl-1H-1,4-benzodiazepine-2,5-dione;7-chloro-3,4-dihydro-4-(2,2-dimethylpropyl)-1H-1,4-benzodiazepine-2,5-dione1,2,3,11a-tetrahydro-3,3,7-trimethyl-5H-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11(10H)-dione;7-bromo-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione;4-tert-butyl-3,4-dihydro-7,9-dimethyl-1H-1,4-benzodiazepine-2,5-dione;4-tert-butyl-7-chloro-3,4-dihydro-2-thio-1H-1,4-benzodiazepine-2,5-dione;4-tert-butyl-7-chloro-3,4-dihydro-9-methyl-1H-1,4-benzodiazepine-2,5-dione;and4-tert-butyl-7-chloro-3,4-dihydro-2-methoxy-5H-1,4-benzodiazepin-5-one.5. The method according to claim 1 which comprises applying saidcompound to the soil, water, or other medium containing seeds or otherpropagating organs of said plants at a rate of about 0.10 kg/ha to 10.0kg/ha.
 6. A method for the selective control of undesirable plantspecies in the presence of cereal crops which comprises applying to thefoliage and stems of the crops and undesirable plant species growing inthe presence thereof or to the soil or water containing seeds or otherpropagating organs of the undesirable plant species in which the cropsare growing, an amount of a compound having the structural formula##STR33## wherein X, X₁, X₂, X₃, A, A₁, W, R, R₁, R₂, R₃ and R₄ are asdescribed in claim 1, effective for the selective control of theundesirable plant species growing in the presence of the crops.
 7. Themethod according to claim 6 wherein X, X₁, X₂, X₃, A, A₁, W, R, R₁, R₂,R₃ and R₄ are as described in claim
 2. 8. The method according to claim7 wherein X, X₁, X₂, X₃, A, A₁, W, R, R₁, R₂, R₃ and R₄ are as describedin claim
 3. 9. The method according to claim 8 wherein the compound isselected from the group consistingof7-chloro-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione, and7-chloro-1,2,3,11a-tetrahydro-3,3-dimethyl-5H-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11(10H)-dione.10. The method according to claim 6 wherein the cereal crops areselected from the group consisting of corn, barley, wheat, oat, rye andrice.
 11. The method according to claim 10 wherein the cereal crop iscorn.
 12. The method according to claim 6 wherein the compound isapplied to the crops and undesirable plant species or to the soil orwater containing seeds or other propagating organs of the undesirableplant species at a rate of about 0.10 kg/ha to 2.5 kg/ha.
 13. Aherbicidal composition which comprises an agronomically acceptablecarrier and a herbicidally effective amount of a compound having thestructural formula ##STR34## wherein X, X1, X2, X₃, A, A₁, W, R, R₁, R₂,R₃ and R₄ are as described in claim
 1. 14. The composition according toclaim 13 wherein X, X₁, X₂, X₃, A, A₁, W, R, R₁, R₂, R₃ and R₄ are asdescribed in claim
 2. 15. The composition according to claim 14 whereinX, X₁, X₂, X₃, A, A₁, W, R, R₁, R₂, R₃ and R₄ are as described in claim3.